Cunningham began publishing a regular series of photographs in the Times in 1978 after a chance photograph of Greta Garbo got the attention of the paper.

After dropping out of Harvard University in 1948, the Boston-born Cunningham moved to New York where he worked as a hat maker and in advertising before being drafted into the US army. After the army, Cunningham returned to New York where he wrote fashion pieces for the Chicago Tribune. He soon segued into photography and started taking photographs of people on the streets before joining the Times.

Bill Cunningham New York – review

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In a 2002 interview with the paper, Cunningham said he always tried to be as discreet as possible because “you get more natural pictures that way.”“I suppose, in a funny way, I’m a record keeper. More than a collector,” he said. “I’m very aware of things not of value but of historical knowledge.”

Cunningham was the subject of a 2010 documentary, Bill Cunningham New York. In 2014, the New-York Historical Society featured a series of photographs Cunningham took long before his images of street fashion became a regular newspaper feature. Taken between 1968 and 1976, he worked on a whimsical photo essay of models in period costumes posing against historic sites of the same vintage.

Astride his bike, he searched secondhand shops for antique clothing and looked for architectural sites across the city to create the perfect tableaux, many of which featured his muse and fellow photographer, Editta Sherman.